Synthesis of homoallylic sulfones through a decarboxylative Claisen rearrangement reaction

被引：37
|
作者：
Bourgeois, D
Craig, D
King, NP
Mountford, DM
机构：
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] GlaxoSmithKline Res Ltd, Neurol & GI Ctr Excellence Drug Discovery, Harlow CM19 5AW, Essex, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 04期
基金：
中国国家自然科学基金;
关键词：
C-C coupling; Claisen rearrangement; homogeneous catalysis; microwave-assisted synthesis; synthetic methods;
D O I：
10.1002/anie.200462023
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A high-yielding preparation of homoallylic sulfones 2 entails the treatment of allylic tosylacetate esters 1 with stoichiometric or substoichiometric quantities of BSA and substoichiometric quantities of KOAc under conventional thermal or microwave conditions. A possible mechanism involves silyl ketene acetal formation, [3,3]-sigmatropic rearrangement, and desilylation- decarboxylation. BSA = N,O-bis(trimethylsilyl)acetamide; Ts = p-toluenesulfonyl.
引用
收藏
页码：618 / 621
页数：4
相关论文
共 50 条
  • [1] Synthesis of homoallylic sulfones via catalytic decarboxylative coupling
    Weaver, Jimmie D.
    Tunge, Jon A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 234
  • [2] Heteroaromatic decarboxylative claisen rearrangement reactions
    Craig, D
    King, NP
    Kley, JT
    Mountford, DM
    SYNTHESIS-STUTTGART, 2005, (19): : 3279 - 3282
  • [3] Transannular, decarboxylative Claisen rearrangement reactions for the synthesis of sulfur-substituted vinylcyclopropanes
    Craig, Donald
    Gore, Sophie J.
    Lansdell, Mark I.
    Lewis, Simon E.
    Mayweg, Alexander V. W.
    White, Andrew J. P.
    CHEMICAL COMMUNICATIONS, 2010, 46 (27) : 4991 - 4993
  • [4] Decarboxylative Claisen rearrangement reactions: synthesis and reactivity of alkylidene-substituted indolines
    Camp, Jason E.
    Craig, Donald
    Funai, Kiyohiko
    White, Andrew J. P.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (22) : 7904 - 7912
  • [5] Decarboxylative claisen rearrangement reactions of allylic tosylmalonate esters
    Craig, D
    Grellepois, F
    ORGANIC LETTERS, 2005, 7 (03) : 463 - 465
  • [6] THERMAL REARRANGEMENT OF CYCLOPROPYL KETONES TO HOMOALLYLIC KETONES . RELATIONSHIP TO ABNORMAL CLAISEN REARRANGEMENT
    ROBERTS, RM
    LANDOLT, RG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (10) : 2281 - &
  • [7] Stereoselective synthesis of allylic sulfones via the oxonia-Cope rearrangement of homoallylic alcohols containing a homoallylic sulfone moiety
    Jung, Se-Young
    Min, Jae-Hong
    Oh, Jung Taek
    Koo, Sangho
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13): : 4823 - 4828
  • [8] SYNTHESIS OF ISOPRENYL CHALCONE SOPHORADIN THROUGH CLAISEN REARRANGEMENT
    KYOGOKU, K
    HATAYAMA, K
    YOKOMORI, S
    SEKI, T
    TANAKA, I
    AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1975, 39 (03): : 667 - 672
  • [9] Reactivity of dearomatised furans synthesised via the decarboxylative Claisen rearrangement
    Camp, Jason E.
    Craig, Donald
    TETRAHEDRON LETTERS, 2009, 50 (26) : 3503 - 3508
  • [10] Double decarboxylative Claisen rearrangement reactions:: microwave-assisted de novo synthesis of pyridines
    Craig, Donald
    Paina, Federica
    Smith, Stephen C.
    CHEMICAL COMMUNICATIONS, 2008, (29) : 3408 - 3410
12345